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Synthesis of Nitrogen‐Containing Derivatives of (18 α ,19 β )‐19‐Hydroxy‐2,3‐secooleanane‐2,3,28‐trioic Acid 28,19‐Lactone
Author(s) -
Shernyukov Andrey V.,
Mainagashev Ilya Ya.,
Korchagina Dina V.,
Genaev Alexander M.,
Komarova Nina I.,
Salakhutdinov Nariman F.,
Tolstikov Genrikh A.
Publication year - 2013
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200492
Subject(s) - chemistry , steric effects , solvent , oxalyl chloride , primary (astronomy) , acid anhydride , nitrogen , lactone , selectivity , organic chemistry , chloride , cyclic amines , medicinal chemistry , amine gas treating , catalysis , physics , astronomy , epoxy
The object of this study is the interaction of the cyclic anhydride 2 of (18 α ,19 β )‐19‐hydroxy‐2,3‐secooleanane‐2,3,28‐trioic acid 28,19‐lactone ( 1 ) with primary and secondary amines. It was shown that the products of steric control (the corresponding 2‐amino‐2‐oxo‐3‐oic acids=2‐amides) were formed solely upon the opening of the anhydride cycle by secondary amines ( Scheme 2 ), whereas the interaction with primary amines yielded a mixture of isomeric amides ( Scheme 10 ). In the latter case, the solvent provided a noticeable effect on the reaction selectivity, which was demonstrated in the case of 4‐methoxybenzylamine. The interaction between the resulting 3‐amides and oxalyl chloride yielded the corresponding cyclic imides, whereas under these conditions, 2‐amides formed spiropyrrolidinetriones ( Scheme 4 ).